Crossdressing Dreams
by NguTheFanfictionWriter
Summary: Kyle's got a secret, which he can't tell anyone about. However as the days go on, can he really keep his secret. Contains BL pairings, also an CanonxOC relationship. (M for Safety)


Kyle sighs, he knew he shouldn't do this any more, but he couldn't help himself. He was paying for it with his money he'd earnt from working part-time, so his mother wouldn't really know. He also had his own credit card and always bought them off Amazon.

Hands shaking, he locks his door and opens the box in front of him. Holding up the items inside the box, he knew his family weren't going to be home for awhile. He removed his clothing, every piece that he had on, apart from his boxers, shaking, he looks at the clothing in the box, last time, he said it would end, but he did it again...

Gulping, he picked up the long wig, and wig caps, placing them on first, the wig matched his natural hair colour, it worked better with his skin. He was glad he cut his hair at the beginning of high school, it was more manageable. Kyle then changed his boxers for panties and a bra, the bra was suited for an A Cup, he grabbed some pads and placed them inside the bra, making an illusion of having breasts.

Blushing slightly, Kyle grabbed the socks, pulling them up to just above his knees, before pulling the skirt on top, then finally grabbing the pink t-shirt, pulling it on and placing the jacket on top of it. He pulled on a pair of plain black slip on shoes with pink bows on, and grabbing the make-up kit, he put on a bit of foundation, then a small amount of blush, eye shadow, lipstick and mascara.

Giving himself a slight turn, he blushed at how well this outfit suited him. Picking up the bag that came with the outfits he bought, he pushed the box into the deepest part of his wardrobe, and finally putting on a scarf.

* * *

Kyle looked around as he walked, blushing and hoping no-one would see it was him, but so far he had been pretty lucky. Smiling contently, he giggled, he couldn't believe how well this was going, how no-one had noticed it was him. He heard some familiar voices.

'_Cartman! Stan, Kenny, Butters and Ngu too! Oh no..._' He burred his face into the scarf, worried that they would see it was him, however they just walked past him pretty much, thinking he got away with it...

"Hey Cutie~ Come here for a second!" Kenny grabbed Kyle's hand and pulled the boy close.

'_Crap!_' He looked at Kenny, nervous, putting on his best girly voice, he smiled nervously "y-yes?"

"What's your name?" Kenny gave a smile. Damn it Kenny! How can you be so seductive!

"K-Kylie." He mentally slapped himself, that was way too close to his real name.

"Hm~!" Kenny smiled, kissing his hand, making the cross dressing boy blush "may I say your eyes sparkle like Emeralds." Kyle blushed.

"Fine Kenny!" Stan sighed "You've proven you can charm anyone."

"So Stan that means you owe Kenny 10 bucks~!" Ngu giggles.

"Damn it..." Stan pulls out 10 dollars and hands it to Kenny. Kenny smirks to himself, placing it in his pocket, kissing Kyle's cheek.

"Sorry Kylie~!" With that, he went to the others, boosting about how easy it was for him to get into any ones pants, with often remarks from Ngu about how he still failed to get into hers properly when they were dating. Which Kyle could see lead to Kenny pouting and Butters blushing.

Kyle sighs, heading home, that was **WAY** too close.

* * *

The next day at school, Kyle sat on his own at lunch, it's been that way ever since he was put into the higher classes. No-one wants to sit with him because he's too smart or too young. He would sit with his old friends, yet they barely had enough room what with the two most popular group in their old school having ended up merging.

Cartman had lost a lot of weight, and now just had a lot of muscle. Kenny was a lot less thin, this was after one night his parents were arrested and were given the death sentence. He and his siblings ended up moving in with Cartman, they help out Cartman and his mother a lot and are really better off. Stan and Wendy finally finished their on and off relationship, Wendy ended up dating Bebe and Stan somehow got together with Kenny. Butters got himself a girlfriend, which lead to his parents grounding him less.

Ngu? You're questioning who she is I'm guessing. She's a student who joint us in Fourth Grade, she ended up dating Kenny. She was a cross dresser pretty much for awhile, until Middle School, then she started dressing slightly more like a girl, losing her boyish outfits. She's currently dating Butters and is also Kenny's go to when he needs cheering up. She pretty much takes care of anyone of us that has a breakdown.

Craig was less of an ass now, he currently is dating Tweek. Crazy right, they get picked on a lot for it, but people understand how good this is for Tweek. The poor guy stopped being as jumpy and has finally started to sleep and ended up calming down quiet fast. He finally stopped jumping and drinking as much coffee. Clyde lost weight as fast as he could, after all he learnt Cartman lost weight and didn't want to be the fattest kid in school, he also cries a lot less and is dating Token. Token is pretty much the same.

Anyways... Kyle is currently sitting on my own, eating my lunch, as he hear footsteps approaching... '_Bullies..._' Kyle shook slightly.

"Hey there smart ass!" The oldest and tallest pushed Kyle onto the floor. "How's having no friends from being such as smart ass!" Kyle just stayed silence "Ah, your such a whore... huh, taking all this pain." He kicked Kyle in the gut. The other boys laughed and joint in yelling harmful names at Kyle and kicking him. Until they heard a familiar shout...

"**Hey!**" Cartman glared at the 3 boys, who just stared back "Leave the Jew **alone**!" The oldest bully went to punch Cartman, but instead punched something like a lead pipe, letting out a few swears

"I'm sorry but physically harming my friends... ends up in you being harmed instead~!" Ngu smiles, swinging the collectable staff she carried fast, hitting the boy in the stomach, sending him onto the ground "we suggest you leave before you get hurt too badly~!" The bullies yelled, running away taking their leader with them.

Cartman pulled Kyle up, muttering something like "stupid Jew." He then pulled Kyle over to the already over crowded table "sit Jew!" he pushed Kyle down in between Kenny and Butters. Ngu handed Kyle his lunch, smiling, instead sitting on Butters lap, which caused the other to blush. Kyle just looked at them with question.

"We kinda were worried about you Kyle, but until today that's never happened where we saw it." Ngu smiles, hugging Kyle slightly, before letting him go "We don't hate you Kyle. We just didn't know what was happening." She smiles.

Kyle just blushed slightly, happy his friends had finally rescued him. But noticed how the table was now over crowded "you guys really should think about getting a better table..."

Kenny blinks, before smirking "Aw but Kyle~ we can easily fix this!" He gets on Stan's lap, smiling at Ngu which caused them both to giggle. Token pulled Clyde onto his lap which caused Clyde to blush, Tweek was worried Craig would do the same but in toll he just flipped off Token, Kenny and Ngu. "See Kyle~" Kyle just sighed.

Tweek looked at Kyle "H-How are yo-you're classes K-Kyle." Kyle smiled back at the boy, happy the other finally could control the outbursts, but sad he still had his stutter.

"Pretty good... I wish that you guys were there though." Everyone just kinda awed but Cartman who shouted "Gay!"

Lunch went pretty good, they all bickered and had some puns and laughs, which ended pervertedly with Kenny pulling down Ngu's top, leading to a hit to his head and some glares from Stan and Butters blushing deeply. Kyle just chuckled.

* * *

School had finished and as Kyle went to walk home, he heard a car pull up "Get in Jew were going shopping." Kyle knew this voice, Cartman, he turned to see everyone in Cartmans car...which was overcrowded... Thinking that inside that car there was 11 people already, and Cartman wanted him to get in

"No-way fatass I won't fit!" Kyle yelled.

"Fucking Jew of course you will!" Cartman turned to Ngu, who opened the door and pulled Kyle onto her lap, giggling "You're body is so skinny you could get between a sandwich!" Cartman finishes, driving off once Ngu closed the door.

Sitting in the front was Cartman (of course) and Kenny with his younger sister Karen on his lap, he was making sure that she was safe. Craig was sat in the very back with Tweek, Token and Clyde. And in the middle was Stan, Kevin, Butters, Ngu and Kyle. Kyle had been moved from Ngu's lap to in between her and Kevin, Butters was currently on Ngu's lap and blushing deeply as she had him close to her chest.

You'd wonder how Cartman fit everyone in there.

At the mall, everyone pretty much stayed together, with there only being two girls in the group and them both being to themselves, they sat and let the boys shop to themselves, when near the end of the trip Cartman turned to them and said it was their turn. Both just smirked, having chatted the entire trip, they pulled the boys into one of the girliest clothing stores in South Park.

The boys looked confused until the girls smiled "Cuz you guys dragged us around, we want a small amount of pay back... Crossdressing time!" Ngu smirked, giggling. Kenny just smirked, giving his alright. Whilst the others groaned.

* * *

Stan was wearing a light blue t-shirt, with a dark blue skirt, knee high black socks, and high heels. Kenny was wearing a light pink dress with a dark pink cardigan, with brown boots. Craig had a black unzipped hoodie with a black tanktop, a black skirt and knee high boots. Tweek had a green knee length summer dress on with dark green sandles. Clyde was wearing a red button up shirt, with dark red shorts and black trainers. Butters was wearing an ocean blue dress with matching sandles. Kevin was wearing a dark pink blouse, with white trousers, and black trainers.

Kyle was different. He had on a knee high black slim dress, with a silver hair band in his hair, a silver belt across the dress, with black high heels. Everyone blushed whilst looking at Kyle. Kenny, Tweek and Butters suited the crossdressing but Kyle... He was a different story.

"Damn Kyle's hot as a girl!" Ngu giggles, being bisexual had perks sometimes, taking pictures of everyone on her phone. Cartman just stared at Kyle.

After everyone finally bought something, the girls had bought Kyle that outfit because he really suited it and it took them forever to convince him to keep it at least. The two had at least come away with some cute clothing for themselves.

They were all currently hanging out at Cartman's house. Kyle rubbed his eyes, feeling sleepy. Cartman looked at Kyle "Oi Jew, sleep." He frowns, throwing a blanket over Kyle "Someone will wake you up when you need to go home." he continues gaming with the rest, whilst Kyle fell into a peaceful sleep.

Kyle felt someone shake him, it was Ngu, he blinks "hm?"

Ngu smiled "Hey Kyle, you're mom called earlier, we told her you were here and she requested that you stayed over, its a weekend and we don't have any thing to do. Cartmans setting up some pillows and blankets in his room so we're all moving up there." She looked to the others who nodded "Stan's gonna carry you up to the room okay?"

Kyle nods, feeling Stan taking him in his arms and taking him upstairs, placing Kyle in one of the make-shift beds Cartman had made, whilst Cartman listed some rules "Rule 1. No having sex in my room. Rule 2. I hear anything I don't like, you're out. Rule 3. No waking anyone up. Be silent kay." Everyone nods. "Good. Now i'm going to sleep so screw you guys." He lay down and fell asleep.

Ngu giggles, getting into one of the beds next to Butters, having Karen next to her, she hugged Karen and kissed the girls forehead, humming a mini lullaby to help her sleep, before moving next to Butters, hugging the boy and falling into a silent slumber.

Kenny and Stan got into the make-shift beds next to Kyle, whilst Kevin went next to his brother. Craig and Tweek went the furthest away from the rest and Token and Clyde went for the last two in the middle. With everyone settled, they then fell asleep.

The next morning Kyle woke up. Smiling slightly,happy to finally have his friends back, but then he thought '_what if they found out._' Panic set in

"Hm... is something wrong?"

* * *

**Alright so this fanfiction minus adding this little bit here was 4 pages long... i'm really proud of myself! :D**

**So this is chapter one. As you can tell, Kyle's into crossdressing and he's afraid of his friends finding out.**

**I find it funny how many people got stuffed into Cartman's car! Lol Yeh, so this uses an main character x oc pairing but I couldn't help it! Butters is so ****cute!**

**For the entire guys crossdressing, should I have a space between each guy or not? 90 days to decide guys! :P**

**Anyways.**

**Leave a review, like or anything if you want. But they would be nice!**

**Cookies for anyone who gets the reference to what cartman said when they were going shopping!**


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